Are there nonstop flights from Kailua-Kona (KOA) to Chicago (MDW)?

No. The fastest connection is via San Jose, about 8h 59m of total flying time.

What is the fastest connection from Kailua-Kona (KOA) to Chicago (MDW)?

via San Jose ≈ 8h 59m, via San Francisco ≈ 8h 59m, via Denver ≈ 8h 59m (estimated flying time, excluding layovers).

Ellison Onizuka Kona International Airport at Keāhole (KOA) to Chicago Midway International Airport (MDW)・6,784 km

No nonstop flights. The fastest connection is via San Jose (SJC), about 8h 59m of flying time (layover not included).

None.

12 one-stop options, sorted by estimated flying time. Tap one to see the airlines on each leg and booking links.

Times are estimated from distance. Check schedules, frequency and availability with the airline or a booking site.